82950-72-9

Basic information

• Product Name: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID
• Synonyms: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID;(S)-1-ACETYLINDOLINE-2-CARBOXYLIC ACID
• CAS NO: 82950-72-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Product Categories: pharmacetical
• Mol File: 82950-72-9.mol

Chemical Properties

• Boiling Point: 494.135°C at 760 mmHg
• Flash Point: 252.644°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID(82950-72-9)
• EPA Substance Registry System: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID(82950-72-9)

Safety Data

• Hazardous Substances Data: 82950-72-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Acetyl-2,3-dihydro-1H-indole-2-carboxylic acid is used as an intermediate for the synthesis of various pharmaceuticals and natural products, contributing to the development of new drugs and therapies.
Used in Cancer Treatment:
(S)-1-Acetyl-2,3-dihydro-1H-indole-2-carboxylic acid is being studied for its potential use in the treatment of cancer, as it has shown biological activities that may be beneficial in combating the disease.
Used in Material Science:
(S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID may have applications in the development of new materials, thanks to its unique chemical structure and properties.
Used in Organic Chemistry:
(S)-1-Acetyl-2,3-dihydro-1H-indole-2-carboxylic acid serves as a building block for the synthesis of complex organic molecules, enabling the creation of novel chemical entities with potential applications in various fields.

InChI:InChI=1/C11H11NO3/c1-7(13)12-9-5-3-2-4-8(9)6-10(12)11(14)15/h2-5,10H,6H2,1H3,(H,14,15)/t10-/m0/s1

Upstream product

• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 108-24-7 acetic anhydride 
• 82923-75-9 N-acetyl-(S)-2,3-dihydro-1H-indole-2-carboxylic acid 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 103476-80-8 1-acetyl-2,3-indoline-2-carboxylic acid 
• 10441-26-6 N-acetyl-indole-2-carboxylic acid 
• 1477-50-5 Indole-2-carboxylic acid 
• 110659-07-9 N-acetyl-indoline-2-carboxylic acid methyl ester 

Downstream Products

• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 82923-75-9 N-acetyl-(S)-2,3-dihydro-1H-indole-2-carboxylic acid 
• 110592-39-7 (S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester 
• 82923-81-7 (S)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester 
• 79854-42-5 Ethyl (S)-indoline-2-carboxylate hydrochloride 
• 82923-76-0 (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride 
• 79815-20-6 (S)-indoline-2-carboxylic acid 

Relevant articles and documents

A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives

A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.

Palladium-Catalyzed Enantioselective Heteroannulation of 1,3-Dienes by Functionally Substituted Aryl Iodides

The first enantioselective heteroannulation of 1,3-dienes by 2-iodoanilines and 2-iodobenzylic alcohols is described. The application of a BINOL-derived phosphoramidite ligand bearing electron-withdrawing substituents is the key to obtaining high enantios

Asymmetric hydrogenation of 2-substituted N-protected-indoles catalyzed by rhodium complexes of BINOL-derived phosphoramidites

The rhodium-catalyzed asymmetric hydrogenation of 2-substituted N-protected-indoles using monodentate phosphoramidites as ligands was examined. Full conversion and 74% ee, were obtained with a catalyst based on PipPhos. The use of a catalytic amount of base is necessary for activity; best results were obtained with Cs2CO3.

Vanishing microwave effects: Influence of heterogeneity

A consistent setup of experiments has been conducted to demonstrate an enhanced reaction rate under microwave irradiation as compared to conventional heating, i.e. a real microwave effect It was found that addition of a cosolvent, diminishing the heterogeneous character of the reaction mixture, greatly reduced the microwave effect. This was demonstrated by two examples; selective mono-urea formation and racemization of an N-acetylamino acid. Furthermore, formation of a Grignard reagent was accelerated under MW irradiation by electrostatic etching of the metal surface. The microwave effect observed in these reactions seems to rely on heterogeneity and specific interactions on the solid-liquid interface. Basic understanding of these findings is crucial for scaling up microwave assisted processes.

NEW PROCESSES FOR THE PREPARATION OF OPTICALLY PURE INDOLINE-2-CARBOXYLIC ACID AND N-ACETYL-INDOLINE-2-CARBOXYLIC ACID

Processes for: a) separating the enantiomers of indoline-2-carboxylic acid of formula (I): comprising of: (i) combining the (R, S) indoline-2-carboxylic acid with (1S)- or (1R)-10- camphorsulfonic acid as the resolving agent in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-indoline-2-carboxylic acid with optically pure (1S)- or (1R)-10-camphorsulfonic acid; (ii) regenerating the (S)- or (R)-indoline-2-carboxylic acid from the crystallized diastereomeric salt by using a suitable base or basic ion-exchange resin; and b) for the optical resolution of N-acetyl-indoline-2-carboxylic acid of formula, (II): comprising of: (i) combining the (R, S)-N-acetyl-indoline-2-carboxylic acid with (S)- or (R)- phenylglycinol as the resolving agent in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-N-acetyl-indoline-2-carboxylic acid with optically pure phenylglycinol; (ii) regenerating the (S)- or (R)-N-acetyl-indoline-2-carboxylic acid from the crystallized salt by using a suitable acid or acidic ion-exchange resin. The non-selected enantiomer may then be racemized and the process (a) or (b) repeated thus to obtain substantial conversion of the material to one enantiomer.

Process for the preparation of an optically active indoline-2-carboxylic acid or derivative thereof

Process for the preparation of an optically active N-acyl-indoline-2-carboxylic acid in which a mixture of enantiomers of N-acyl-indoline-carboxylic acid is contacted with an optically active resolving agent and the optically active N-acyl-indoline-2-carboxylic acid is liberated from the resulting diastereomeric salt, as resolving agent use being made of a compound of formula 1, where R1 represents an alkyl group and R2 a hetero-aryl group or where R1 and R2 together with the C atoms to which they are bound form a cycloalkyl group with 5-8 C atoms, fused with a hetero-aryl group. Preferably, a mixture of enantiomers of an N-acyl-indoline-2-carboxylic acid is prepared in a process comprising the steps of Fischer indole cyclization of a 2-phenylhydrazone propionic acid or a derivative thereof in the presence of an acid catalyst, if necessary hydrolysis of the derivative to the corresponding acid, acylation at the N-position and reduction of the indole compound to the corresponding indoline compound, after which the resulting N-acyl-indoline-2-carboxylic acid is subjected to the resolution. The 2-phenylhydrazonopropionic acid or a derivative thereof is preferably obtained from phenylhydrazine and pyruvic acid or the corresponding derivative thereof.

Direct Optical Resolution of Carboxylic Acids by Chyral HPLC on Tris(3,5-dimethylphenylcarbamate)s of Cellulose and Amylose

A variety of racemic carboxylic acids have been for the first time directly resolved by normal-phase, high-performance liquid chromatography using a hexane-2-propanol eluting system containing a small amount (ca. 1percent) of a strong carboxylic acid, like formic acid, trichloroacetic acid, and trifluoroacetic acid.

Application of Microbes and Microbial Esterases to the Preparation of Optically Active N-Acetylindoline-2-Carboxylic Acid

Methylotrophic bacteria, isolated from soil samples or from sewage sludge, proved to be useful sources of esterases for catalyzing the enantioselective hydrolysis of racemic N-acetyl-indoline-2-carboxylic acid methyl ester (7) to the corresponding (2S) or (2R)-N-acetyl amino acid (6) with high optical yields.From the DMF-utilizer Pseudomonas DMF 5/8 and the methanol-utilizer Isolate EE 210, the corresponding esterases were isolated.Reactions with whole cells as well as with the purified enzymes are described.

1-(carbamyl, thiocarbamyl, and iminocarbamyl)-indoline derivatives

1-(Carbamyl, thiocarbamyl, and iminocarbamyl)-indoline derivatives of the formula STR1 where each R1 is independently alkyl, alkoxy, acyloxy, hydroxy, halo or trifluoromethyl, n is 0, 1, 2 or 3, R2 and R3 are independently hydroxy, alkoxy, amino or substituted amino, R4 and R5 are independently hydrogen, alkyl or substituted alkyl, R6 is hydrogen, alkyl or substituted alkyl, and Y is O, S or N--R7 where R7 is hydrogen, alkyl, cyano or substituted alkyl, and salts thereof, which are useful as antihypertensive and cardioactive agents, methods of preparing the same, and pharmaceutical compositions thereof, are provided.

1-mercaptoalkanoylindoline-2-carboxylic acids

1-Mercaptoalkanoylindoline-2-carboxylic acids, e.g., those of the formula STR1 and functional derivatives thereof, are antihypertensive and cardioactive agents.